Acetonitrile → 3-Amino-3-(4-chlorophenyl)prop-2-enenitrile

HRID 128164Notes

Reaction equation

HRID 128164 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:12](#[N:14])[CH3:13]>CCOCC.O.CO.C(O)(C)C>[NH2:7][C:6]([C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH:13][C:12]#[N:14]

Participants

8

Reactant 3

HCID 6342AcetonitrileHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 14848883-Amino-3-(4-chlorophenyl)prop-2-enenitrile

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolvent

Procedure

To a mixture of 68.5 g of p-chlorobenzonitrile and 24.0 g. of sodium hydride (50% in mineral oil) in 250 ml. of ether is added, 26.1 ml. of acetonitrile and 2 ml. of isopropanol. The mixture is stirred and refluxed on a steam bath for 6 hours and then stirred overnight at room temperature. A 5 ml. portion of methanol and 250 ml. of water are added. The ether is boiled away on a steam bath and the mixture is filtered. The solid is dissolved in warm ethyl acetate and filtered. The filtrate is evaporated to a solid giving β-amino-4-chlorocinnamonitrile.

Workup

  1. temperaturerefluxed on a steam bath for 6 hours
  2. stirringstirred overnight at room temperature
  3. filtrationthe mixture is filtered
  4. dissolutionThe solid is dissolved in warm ethyl acetate
  5. filtrationfiltered
  6. customThe filtrate is evaporated to a solid

Sources & evidence

ORD record
ord-7fc2607daff448fcb282320d75af278a
Source dataset
uspto-grants-1981_03
Patent number
US04259256

Reaction notes

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